The smart cities of the future are expected to be serviced by advanced, personalized multimodal transit systems, charged with timely transport of citizens. Optimizing routes on such networks is a complex problem, in part due to the fact that simple metrics such as latency by themselves are not sufficient to find the best routes. In this paper, we focus on the problem of providing commuters with personalized routes with the most convenience. We present our mathematical model of user convenience during a multi-leg journey, and the overview of a middleware for enabling convenient transit (including ensuring acceptable network connectivity to mobile apps) by using crowdsourcing. We also report on initial insights obtained through empirical studies on network connectivity and user-perception of convenience in Delhi, India, and Paris, France.